Southend United on 13 July 2005. He joined Southend for an undisclosed fee. He made his Southend debut in the club's opening match of the 2005–06 season, starting in a 2–1 defeat against Port Vale at Roots Hall. He stated similarities between Southend manager Steve Tilson and previous manager Stimson meant he settled in quickly at Southend. He played 31 times for the club during the season. He scored his only Southend goal in a 3–1 win over rivals Colchester United, and helped Southend achieve promotion to the Championship. Having made two appearances for Southend in the opening month of the 2006–07 season, Cole felt he needed more game-time. Whilst Tilson did not want him to go, he agreed to loan out Cole to League One club Northampton Town for a month. Cole made his Northampton debut in a 3–1 defeat against Tranmere Rovers at Sixfields. He scored his first goal for Northampton against Millwall in a 1–0 away victory on 24 September 2006. His loan agreement at Northampton was extended for a further month on 11 October 2006, and he went on to play nine times during his time with the club. He returned to Southend in November 2006, and made three more appearances for the club before his run was curtailed by injury. Stevenage Cole subsequently joined Conference Premier club Stevenage Borough for a five-figure fee on 26 January 2007. The move reunited him with manager Mark Stimson, who had previously managed him at Grays. He made his Stevenage debut as a substitute in a 1–1 draw at Stonebridge Road against Ebbsfleet United on 28 January 2007. Cole went on to make 22 more appearances during the 2006–07 season, scoring three times; his first goal for the club coming in a 4–4 away draw against Forest Green Rovers on 9 April 2007. Cole scored Stevenage's first goal in a 3–2 victory in the FA Trophy final against Kidderminster Harriers at Wembley Stadium in front of 53,262 spectators, a game in which Stevenage came from two goals behind to become the first team to win a competitive final at the new stadium. Cole's goal came just after half-time; collecting Steve Morison's flick-on before finishing calmly. At the start of the 2007–08 season, Cole suffered a knee injury in Stevenage's victory against Histon, which meant he missed the next six weeks of the season. He scored two goals in 27